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Volume 69 
Part 12 
Pages o1802-o1803  
December 2013  

Received 13 November 2013
Accepted 16 November 2013
Online 23 November 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.052
wR = 0.133
Data-to-parameter ratio = 33.5
Details
Open access

1-(2-Bromo­meth­yl-1-phenyl­sulfonyl-1H-indol-3-yl)propan-1-one

aResearch Scholar (Chemistry), Bharathiyar University, Coimbatore 641 046, Tamilnadu, India,bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India,cDepartment of Sciences, Chemistry and Materials Research Lab, Amrita Vishwa Vidyapeetham University, Ettimadai, Coimbatore 641 112, India, and dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
Correspondence e-mail: ryamuna1@gmail.com, chakkaravarthi_2005@yahoo.com

In the title compound, C18H16BrNO3S, the dihedral angle between the phenyl ring and the indole ring system is 89.91 (11)°. The mol­ecular structure features weak C-H...O and C-H...Br hydrogen bonds. In the crystal, mol­ecules are linked by weak C-H...O hydrogen bonds, forming chains along the a-axis direction. The chains are further linked by C-H...[pi] inter­actions, forming a layer parallel to the ab plane.

Related literature

For the biological activity of indole derivatives, see: Chai et al. (2006[Chai, H., Zhao, C. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911-917.]); Nieto et al. (2005[Nieto, M. J., Alovero, F. L., Manzo, R. H. & Mazzieri, M. R. (2005). Eur. J. Med. Chem. 40, 361-369.]). For related structures, see: Chakkaravarthi et al. (2008[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o749.], 2010[Chakkaravarthi, G., Panchatcharam, R., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2010). Acta Cryst. E66, o2957.]). For details of the configuration at the S atom, see: Bassindale (1984[Bassindale, A. (1984). In The Third Dimension in Organic Chemistry. New York: John Wiley and Sons.]). For details of N-atom hybridization, see: Beddoes et al. (1986[Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787-797.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16BrNO3S

  • Mr = 406.29

  • Monoclinic, P 21 /c

  • a = 10.2772 (7) Å

  • b = 8.6610 (6) Å

  • c = 18.8980 (14) Å

  • [beta] = 90.676 (2)°

  • V = 1682.0 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.58 mm-1

  • T = 295 K

  • 0.38 × 0.34 × 0.30 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.397, Tmax = 0.461

  • 25944 measured reflections

  • 7303 independent reflections

  • 3726 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.133

  • S = 1.00

  • 7303 reflections

  • 218 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.11 e Å-3

  • [Delta][rho]min = -0.90 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1-C6 and C9-C14 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C6-H6...Br1 0.93 2.89 3.815 (2) 171
C13-H13...O2 0.93 2.39 2.978 (3) 121
C15-H15B...O1 0.97 2.15 2.833 (3) 126
C2-H2...O3i 0.93 2.59 3.191 (3) 123
C15-H15A...Cg3ii 0.97 2.74 3.486 (3) 134
C18-H18B...Cg2iii 0.96 2.66 3.616 (3) 174
Symmetry codes: (i) x+1, y, z; (ii) -x, -y+1, -z+2; (iii) -x, -y, -z+2.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5323 ).


Acknowledgements

The authors wish to acknowledge the SAIF, IIT, Madras, for the data collection.

References

Bassindale, A. (1984). In The Third Dimension in Organic Chemistry. New York: John Wiley and Sons.
Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787-797.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chai, H., Zhao, C. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911-917.  [CrossRef] [PubMed] [ChemPort]
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o749.  [CSD] [CrossRef] [IUCr Journals]
Chakkaravarthi, G., Panchatcharam, R., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2010). Acta Cryst. E66, o2957.  [CSD] [CrossRef] [IUCr Journals]
Nieto, M. J., Alovero, F. L., Manzo, R. H. & Mazzieri, M. R. (2005). Eur. J. Med. Chem. 40, 361-369.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1802-o1803   [ doi:10.1107/S1600536813031413 ]

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